Enantioselective acylation of secondary alcohols catalyzed by chiral N-heterocyclic carbenes

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1347-1349

  Kano, Taichi ^a   Sasaki, Kouji ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND; LIGAND; TRANSITION ELEMENT;

ACYLATION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY;

EID: 17444417515     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050174r     Document Type: Article

References (51)

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38. 4-Aminopyridine: (a) Fu, G. C. Acc. Chem. Res. 2000, 33, 412. (b) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. (c) Spivey, A. C.; Zhu, F.; Mitchell, M. B.; Davey, S. G.; Jarvest, R. L. J. Org. Chem. 2003, 68, 7379. (d) Priem, G.; Pelotier, B.; Macdonald, S. J. F.; Anson, M. S.; Campbell, I. B. J. Org. Chem. 2003, 68, 3844.
39. 4-Aminopyridine: (a) Fu, G. C. Acc. Chem. Res. 2000, 33, 412. (b) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. (c) Spivey, A. C.; Zhu, F.; Mitchell, M. B.; Davey, S. G.; Jarvest, R. L. J. Org. Chem. 2003, 68, 7379. (d) Priem, G.; Pelotier, B.; Macdonald, S. J. F.; Anson, M. S.; Campbell, I. B. J. Org. Chem. 2003, 68, 3844.
40. 4-Aminopyridine: (a) Fu, G. C. Acc. Chem. Res. 2000, 33, 412. (b) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. (c) Spivey, A. C.; Zhu, F.; Mitchell, M. B.; Davey, S. G.; Jarvest, R. L. J. Org. Chem. 2003, 68, 7379. (d) Priem, G.; Pelotier, B.; Macdonald, S. J. F.; Anson, M. S.; Campbell, I. B. J. Org. Chem. 2003, 68, 3844.
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49. Vinyl diphenylacetate is readily prepared from diphenylacetic acid and vinyl acetate. See the Supporting Information for details.
50. The resulting 1-phenylethyl diphenylacetate is readily hydrolyzed with aqueous NaOH to 1-phenylethanol without loss of enantiopurity.
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